BRPI0711208A2 - compostos, intermediários para a sìtemse dos compostos, processo, composição farmacêutica, uso de um composto e usos - Google Patents
compostos, intermediários para a sìtemse dos compostos, processo, composição farmacêutica, uso de um composto e usos Download PDFInfo
- Publication number
- BRPI0711208A2 BRPI0711208A2 BRPI0711208-4A BRPI0711208A BRPI0711208A2 BR PI0711208 A2 BRPI0711208 A2 BR PI0711208A2 BR PI0711208 A BRPI0711208 A BR PI0711208A BR PI0711208 A2 BRPI0711208 A2 BR PI0711208A2
- Authority
- BR
- Brazil
- Prior art keywords
- phenyl
- group
- methoxy
- piperidin
- formula
- Prior art date
Links
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- 230000015572 biosynthetic process Effects 0.000 title claims abstract description 12
- 238000003786 synthesis reaction Methods 0.000 title claims abstract description 9
- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 6
- 239000000543 intermediate Substances 0.000 title claims description 35
- 238000000034 method Methods 0.000 title abstract description 146
- 230000008569 process Effects 0.000 title abstract description 23
- -1 monoalkylamino Chemical group 0.000 claims abstract description 225
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 124
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- 125000001188 haloalkyl group Chemical group 0.000 claims abstract description 74
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 57
- 125000004663 dialkyl amino group Chemical group 0.000 claims abstract description 40
- 125000004438 haloalkoxy group Chemical group 0.000 claims abstract description 40
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 34
- 125000004995 haloalkylthio group Chemical group 0.000 claims abstract description 32
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 32
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 31
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims abstract description 31
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 30
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 27
- 229940002612 prodrug Drugs 0.000 claims abstract description 16
- 239000000651 prodrug Substances 0.000 claims abstract description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 11
- 239000001257 hydrogen Substances 0.000 claims abstract description 11
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 10
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 7
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- 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 77
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 63
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 22
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- 238000006243 chemical reaction Methods 0.000 claims description 19
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- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 16
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- 125000004043 oxo group Chemical group O=* 0.000 claims description 8
- 125000004863 4-trifluoromethoxyphenyl group Chemical group [H]C1=C([H])C(OC(F)(F)F)=C([H])C([H])=C1* 0.000 claims description 7
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- 208000025009 anogenital human papillomavirus infection Diseases 0.000 claims description 7
- 201000004201 anogenital venereal wart Diseases 0.000 claims description 7
- 125000004185 ester group Chemical group 0.000 claims description 7
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 7
- 229920002554 vinyl polymer Polymers 0.000 claims description 7
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 6
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 6
- 125000004442 acylamino group Chemical group 0.000 claims description 6
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 6
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- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 6
- 230000007062 hydrolysis Effects 0.000 claims description 6
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- 125000003386 piperidinyl group Chemical group 0.000 claims description 6
- 125000006239 protecting group Chemical group 0.000 claims description 6
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims description 5
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- 206010028980 Neoplasm Diseases 0.000 claims description 5
- 125000004945 acylaminoalkyl group Chemical group 0.000 claims description 5
- 125000001246 bromo group Chemical group Br* 0.000 claims description 5
- 125000004122 cyclic group Chemical group 0.000 claims description 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 5
- 125000005541 phosphonamide group Chemical group 0.000 claims description 5
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 claims description 5
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- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 4
- 230000008021 deposition Effects 0.000 claims description 4
- 208000003154 papilloma Diseases 0.000 claims description 4
- 150000003536 tetrazoles Chemical class 0.000 claims description 4
- 125000006497 3-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C(OC([H])([H])[H])=C1[H])C([H])([H])* 0.000 claims description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 3
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- 238000010511 deprotection reaction Methods 0.000 claims description 3
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- 125000004434 sulfur atom Chemical group 0.000 claims description 3
- 201000009030 Carcinoma Diseases 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 125000004193 piperazinyl group Chemical group 0.000 claims description 2
- XUWHAWMETYGRKB-UHFFFAOYSA-N piperidin-2-one Chemical compound O=C1CCCCN1 XUWHAWMETYGRKB-UHFFFAOYSA-N 0.000 claims description 2
- 230000009385 viral infection Effects 0.000 claims description 2
- 239000005711 Benzoic acid Substances 0.000 claims 3
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- 235000007265 Myrrhis odorata Nutrition 0.000 claims 1
- CWRVKFFCRWGWCS-UHFFFAOYSA-N Pentrazole Chemical compound C1CCCCC2=NN=NN21 CWRVKFFCRWGWCS-UHFFFAOYSA-N 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 abstract description 2
- 150000002367 halogens Chemical class 0.000 abstract description 2
- 150000002431 hydrogen Chemical group 0.000 abstract 2
- 239000004215 Carbon black (E152) Substances 0.000 abstract 1
- 229940124686 HPV inhibitor Drugs 0.000 abstract 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 239000000047 product Substances 0.000 description 286
- 238000004611 spectroscopical analysis Methods 0.000 description 145
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 141
- 238000004128 high performance liquid chromatography Methods 0.000 description 139
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 128
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 92
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 88
- 238000005160 1H NMR spectroscopy Methods 0.000 description 86
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 78
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- 229910052943 magnesium sulfate Inorganic materials 0.000 description 27
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- 239000012280 lithium aluminium hydride Substances 0.000 description 25
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- BOLQPGRSJMIKMA-UHFFFAOYSA-N n-(4-benzylphenyl)-2-piperidin-1-ylaniline Chemical compound C=1C=C(NC=2C(=CC=CC=2)N2CCCCC2)C=CC=1CC1=CC=CC=C1 BOLQPGRSJMIKMA-UHFFFAOYSA-N 0.000 description 1
- UPPLMUAPDBEEFM-UHFFFAOYSA-N n-(4-bromo-3-methylphenyl)-2-methyl-6-nitroaniline Chemical compound C1=C(Br)C(C)=CC(NC=2C(=CC=CC=2C)[N+]([O-])=O)=C1 UPPLMUAPDBEEFM-UHFFFAOYSA-N 0.000 description 1
- LJVBGRFALKNDJE-UHFFFAOYSA-N n-(4-bromophenyl)-2-methyl-6-nitroaniline Chemical compound CC1=CC=CC([N+]([O-])=O)=C1NC1=CC=C(Br)C=C1 LJVBGRFALKNDJE-UHFFFAOYSA-N 0.000 description 1
- SCFLEFDPFFBFPT-UHFFFAOYSA-N n-(4-bromophenyl)-2-methyl-6-piperidin-1-ylaniline Chemical compound C=1C=C(Br)C=CC=1NC=1C(C)=CC=CC=1N1CCCCC1 SCFLEFDPFFBFPT-UHFFFAOYSA-N 0.000 description 1
- GMFUKKONFZISMI-UHFFFAOYSA-N n-(4-bromophenyl)-2-nitroaniline Chemical compound [O-][N+](=O)C1=CC=CC=C1NC1=CC=C(Br)C=C1 GMFUKKONFZISMI-UHFFFAOYSA-N 0.000 description 1
- XCCAWJIMKYHDSC-UHFFFAOYSA-N n-(4-cyclohexyloxyphenyl)-2-nitroaniline Chemical compound [O-][N+](=O)C1=CC=CC=C1NC(C=C1)=CC=C1OC1CCCCC1 XCCAWJIMKYHDSC-UHFFFAOYSA-N 0.000 description 1
- WYXDSPMRWCZSRJ-UHFFFAOYSA-N n-(4-cyclohexyloxyphenyl)-2-piperidin-1-ylaniline Chemical compound C1CCCCC1OC(C=C1)=CC=C1NC1=CC=CC=C1N1CCCCC1 WYXDSPMRWCZSRJ-UHFFFAOYSA-N 0.000 description 1
- CWRPCBMKIREHDB-UHFFFAOYSA-N n-(4-cyclohexylphenyl)-2-nitroaniline Chemical compound [O-][N+](=O)C1=CC=CC=C1NC1=CC=C(C2CCCCC2)C=C1 CWRPCBMKIREHDB-UHFFFAOYSA-N 0.000 description 1
- IGRCXXAANLZZNB-UHFFFAOYSA-N n-(4-cyclohexylphenyl)-2-piperidin-1-ylaniline Chemical compound C1CCCCC1C(C=C1)=CC=C1NC1=CC=CC=C1N1CCCCC1 IGRCXXAANLZZNB-UHFFFAOYSA-N 0.000 description 1
- ROPBEHWHXADACY-UHFFFAOYSA-N n-(4-methoxyphenyl)-2-methyl-6-piperidin-1-ylaniline Chemical compound C1=CC(OC)=CC=C1NC1=C(C)C=CC=C1N1CCCCC1 ROPBEHWHXADACY-UHFFFAOYSA-N 0.000 description 1
- JLIRPISIPQMEDU-UHFFFAOYSA-N n-(4-methoxyphenyl)-2-nitroaniline Chemical compound C1=CC(OC)=CC=C1NC1=CC=CC=C1[N+]([O-])=O JLIRPISIPQMEDU-UHFFFAOYSA-N 0.000 description 1
- CNSRDKAUPIRUDA-UHFFFAOYSA-N n-(4-methoxyphenyl)-2-piperidin-1-ylaniline Chemical compound C1=CC(OC)=CC=C1NC1=CC=CC=C1N1CCCCC1 CNSRDKAUPIRUDA-UHFFFAOYSA-N 0.000 description 1
- MZZAKYDRNCNQHW-UHFFFAOYSA-N n-(4-phenoxyphenyl)-2-piperidin-1-ylaniline Chemical compound C1CCCCN1C1=CC=CC=C1NC(C=C1)=CC=C1OC1=CC=CC=C1 MZZAKYDRNCNQHW-UHFFFAOYSA-N 0.000 description 1
- NJFFGHDUIISOHY-UHFFFAOYSA-N n-(4-phenylsulfanylphenyl)-2-piperidin-1-ylaniline Chemical compound C1CCCCN1C1=CC=CC=C1NC(C=C1)=CC=C1SC1=CC=CC=C1 NJFFGHDUIISOHY-UHFFFAOYSA-N 0.000 description 1
- QDEQSRMGTXMRFW-UHFFFAOYSA-N n-[(4-methoxyphenyl)methyl]-2-piperidin-1-ylaniline Chemical compound C1=CC(OC)=CC=C1CNC1=CC=CC=C1N1CCCCC1 QDEQSRMGTXMRFW-UHFFFAOYSA-N 0.000 description 1
- IDCIJOMKARADSP-UHFFFAOYSA-N n-[2-(4-methoxyphenyl)ethyl]-2-piperidin-1-ylaniline Chemical compound C1=CC(OC)=CC=C1CCNC1=CC=CC=C1N1CCCCC1 IDCIJOMKARADSP-UHFFFAOYSA-N 0.000 description 1
- IYOCRRUYBMKMCM-UHFFFAOYSA-N n-[4-(4-chlorophenoxy)phenyl]-2-nitroaniline Chemical compound [O-][N+](=O)C1=CC=CC=C1NC(C=C1)=CC=C1OC1=CC=C(Cl)C=C1 IYOCRRUYBMKMCM-UHFFFAOYSA-N 0.000 description 1
- NWWLANJHGWJDKW-UHFFFAOYSA-N n-[4-(4-chlorophenoxy)phenyl]-2-piperidin-1-ylaniline Chemical compound C1=CC(Cl)=CC=C1OC(C=C1)=CC=C1NC1=CC=CC=C1N1CCCCC1 NWWLANJHGWJDKW-UHFFFAOYSA-N 0.000 description 1
- PRUCYNIICGAELI-UHFFFAOYSA-N n-[4-(4-fluorophenoxy)phenyl]-2-methyl-6-nitroaniline Chemical compound CC1=CC=CC([N+]([O-])=O)=C1NC(C=C1)=CC=C1OC1=CC=C(F)C=C1 PRUCYNIICGAELI-UHFFFAOYSA-N 0.000 description 1
- LWIJZAOBUPWGRC-UHFFFAOYSA-N n-[4-(4-fluorophenoxy)phenyl]-2-methyl-6-piperidin-1-ylaniline Chemical compound C=1C=C(OC=2C=CC(F)=CC=2)C=CC=1NC=1C(C)=CC=CC=1N1CCCCC1 LWIJZAOBUPWGRC-UHFFFAOYSA-N 0.000 description 1
- CMVZNINJTVALHA-UHFFFAOYSA-N n-[4-(4-fluorophenoxy)phenyl]-2-nitroaniline Chemical compound [O-][N+](=O)C1=CC=CC=C1NC(C=C1)=CC=C1OC1=CC=C(F)C=C1 CMVZNINJTVALHA-UHFFFAOYSA-N 0.000 description 1
- PEZYSHSSQRUDJG-UHFFFAOYSA-N n-[4-(4-fluorophenoxy)phenyl]-2-piperidin-1-ylaniline Chemical compound C1=CC(F)=CC=C1OC(C=C1)=CC=C1NC1=CC=CC=C1N1CCCCC1 PEZYSHSSQRUDJG-UHFFFAOYSA-N 0.000 description 1
- MCRHCJGYRXSHEP-UHFFFAOYSA-N n-[4-(4-methoxyphenyl)phenyl]-2-methyl-6-piperidin-1-ylaniline Chemical compound C1=CC(OC)=CC=C1C(C=C1)=CC=C1NC1=C(C)C=CC=C1N1CCCCC1 MCRHCJGYRXSHEP-UHFFFAOYSA-N 0.000 description 1
- IAGQQSXQAOPMEA-UHFFFAOYSA-N n-[4-(4-methoxyphenyl)phenyl]-2-piperidin-1-ylaniline Chemical compound C1=CC(OC)=CC=C1C(C=C1)=CC=C1NC1=CC=CC=C1N1CCCCC1 IAGQQSXQAOPMEA-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 230000005305 organ development Effects 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 208000029211 papillomatosis Diseases 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 238000005897 peptide coupling reaction Methods 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- NCZQECUWKXITOE-UHFFFAOYSA-N phenyl-[4-(2-piperidin-1-ylanilino)phenyl]methanone Chemical compound C=1C=C(NC=2C(=CC=CC=2)N2CCCCC2)C=CC=1C(=O)C1=CC=CC=C1 NCZQECUWKXITOE-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 125000005633 phthalidyl group Chemical group 0.000 description 1
- 125000005936 piperidyl group Chemical group 0.000 description 1
- 229940068585 podofilox Drugs 0.000 description 1
- 229940068582 podophyllin Drugs 0.000 description 1
- YJGVMLPVUAXIQN-XVVDYKMHSA-N podophyllotoxin Chemical compound COC1=C(OC)C(OC)=CC([C@@H]2C3=CC=4OCOC=4C=C3[C@H](O)[C@@H]3[C@@H]2C(OC3)=O)=C1 YJGVMLPVUAXIQN-XVVDYKMHSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 210000000664 rectum Anatomy 0.000 description 1
- 230000000306 recurrent effect Effects 0.000 description 1
- 230000022532 regulation of transcription, DNA-dependent Effects 0.000 description 1
- 230000000241 respiratory effect Effects 0.000 description 1
- 210000002345 respiratory system Anatomy 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 206010040882 skin lesion Diseases 0.000 description 1
- 231100000444 skin lesion Toxicity 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical class [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- DUDQEUATMXJHPB-UHFFFAOYSA-N tert-butyl n-amino-n-(2-methyl-6-nitrophenyl)carbamate Chemical compound CC1=CC=CC([N+]([O-])=O)=C1N(N)C(=O)OC(C)(C)C DUDQEUATMXJHPB-UHFFFAOYSA-N 0.000 description 1
- DKACXUFSLUYRFU-UHFFFAOYSA-N tert-butyl n-aminocarbamate Chemical compound CC(C)(C)OC(=O)NN DKACXUFSLUYRFU-UHFFFAOYSA-N 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 125000000464 thioxo group Chemical group S=* 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 230000002103 transcriptional effect Effects 0.000 description 1
- 238000001890 transfection Methods 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 125000002827 triflate group Chemical group FC(S(=O)(=O)O*)(F)F 0.000 description 1
- 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- UCPYLLCMEDAXFR-UHFFFAOYSA-N triphosgene Chemical compound ClC(Cl)(Cl)OC(=O)OC(Cl)(Cl)Cl UCPYLLCMEDAXFR-UHFFFAOYSA-N 0.000 description 1
- 241001529453 unidentified herpesvirus Species 0.000 description 1
- 241000712461 unidentified influenza virus Species 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 244000052613 viral pathogen Species 0.000 description 1
- 210000002845 virion Anatomy 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/12—Keratolytics, e.g. wart or anti-corn preparations
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/20—Antivirals for DNA viruses
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
- C07D295/135—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Virology (AREA)
- Epidemiology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Dermatology (AREA)
- Biotechnology (AREA)
- Molecular Biology (AREA)
- Pulmonology (AREA)
- Endocrinology (AREA)
- Reproductive Health (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0604496A FR2901273B1 (fr) | 2006-05-19 | 2006-05-19 | Inhibiteurs du virus du papillome humain et les compositions pharmaceutiques les contenant |
| FR0604496 | 2006-05-19 | ||
| PCT/EP2007/054843 WO2007135106A1 (fr) | 2006-05-19 | 2007-05-18 | Derives de piperidine comme inhibiteurs du virus du papillome humain |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BRPI0711208A2 true BRPI0711208A2 (pt) | 2011-03-22 |
Family
ID=37575135
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BRPI0711208-4A BRPI0711208A2 (pt) | 2006-05-19 | 2007-05-18 | compostos, intermediários para a sìtemse dos compostos, processo, composição farmacêutica, uso de um composto e usos |
Country Status (13)
| Country | Link |
|---|---|
| US (3) | US8207373B2 (enExample) |
| EP (1) | EP2024350B1 (enExample) |
| JP (1) | JP5399237B2 (enExample) |
| CN (1) | CN101466693B (enExample) |
| AR (1) | AR061027A1 (enExample) |
| BR (1) | BRPI0711208A2 (enExample) |
| CA (1) | CA2652469C (enExample) |
| DK (1) | DK2024350T3 (enExample) |
| ES (1) | ES2436772T3 (enExample) |
| FR (1) | FR2901273B1 (enExample) |
| MX (1) | MX2008014771A (enExample) |
| PT (1) | PT2024350E (enExample) |
| WO (1) | WO2007135106A1 (enExample) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2923825B1 (fr) * | 2007-11-20 | 2013-05-03 | Anaconda Pharma | Nouveaux inhibiteurs du virus du papillome humain et les compositions pharmaceutiques les contenant. |
| FR2990134B1 (fr) * | 2012-05-07 | 2014-11-21 | Anaconda Pharma | Composition pharmaceutique d'un inhibiteur du virus du papillome |
| FR3000490B1 (fr) | 2012-12-27 | 2015-03-13 | Anaconda Pharma | Procede de synthese d'une hydrazine utile dans le traitement du virus du papillome |
| ES2796276T3 (es) * | 2015-02-05 | 2020-11-26 | Ab Science | Compuestos con actividad antitumoral |
| WO2017009751A1 (en) | 2015-07-15 | 2017-01-19 | Pfizer Inc. | Pyrimidine derivatives |
| CN105582083A (zh) * | 2015-09-08 | 2016-05-18 | 石友爱 | 一种治疗鲍温样丘疹病的中药 |
| CN108530310B (zh) * | 2017-03-02 | 2025-01-28 | 中国科学院上海药物研究所 | 2-(取代苯杂基)芳香甲酸类fto抑制剂，其制备方法及其应用 |
| CN109748903B (zh) * | 2017-11-01 | 2021-08-10 | 北京协和制药二厂 | 吡法齐明的制备方法 |
| EP3594206A1 (en) | 2018-07-09 | 2020-01-15 | Abivax | Phenyl-n-quinoline derivatives for treating a rna virus infection |
| EP3594205A1 (en) | 2018-07-09 | 2020-01-15 | Abivax | Phenyl-n-aryl derivatives for treating a rna virus infection |
| JP2020127293A (ja) * | 2019-02-05 | 2020-08-20 | ファナック株式会社 | ロータコアの製造装置及びロータコアの製造方法、並びにロータ構造 |
| CN110041223B (zh) * | 2019-06-03 | 2021-10-22 | 西北师范大学 | 以肼类化合物为原料氧化合成偶氮类化合物的方法 |
| EP3999493B1 (en) | 2019-07-19 | 2023-12-20 | Abivax | Aryl-n-aryl derivatives for treating a rna virus infection |
| CN114276273B (zh) * | 2021-12-29 | 2024-06-21 | 维思普新材料（苏州）有限公司 | 一种基于四苯基肼类衍生物的有机电致发光材料及其电子器件 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4292429A (en) * | 1978-03-08 | 1981-09-29 | Ciba-Geigy Corporation | Imidazole urea and amido compounds |
| CZ301802B6 (cs) * | 1999-03-19 | 2010-06-30 | Vertex Pharmaceuticals Incorporated | Deriváty mocoviny jako inhibitory IMPDH a farmaceutické prostredky s jejich obsahem |
| CA2526506A1 (en) * | 2003-06-09 | 2004-12-16 | Boehringer Ingelheim International Gmbh | Inhibitors of papilloma virus |
-
2006
- 2006-05-19 FR FR0604496A patent/FR2901273B1/fr not_active Expired - Fee Related
-
2007
- 2007-05-18 JP JP2009511485A patent/JP5399237B2/ja not_active Expired - Fee Related
- 2007-05-18 EP EP07729287.8A patent/EP2024350B1/fr not_active Not-in-force
- 2007-05-18 MX MX2008014771A patent/MX2008014771A/es active IP Right Grant
- 2007-05-18 PT PT77292878T patent/PT2024350E/pt unknown
- 2007-05-18 US US12/300,998 patent/US8207373B2/en not_active Expired - Fee Related
- 2007-05-18 ES ES07729287.8T patent/ES2436772T3/es active Active
- 2007-05-18 AR ARP070102162A patent/AR061027A1/es not_active Application Discontinuation
- 2007-05-18 CN CN2007800218616A patent/CN101466693B/zh not_active Expired - Fee Related
- 2007-05-18 BR BRPI0711208-4A patent/BRPI0711208A2/pt not_active IP Right Cessation
- 2007-05-18 DK DK07729287.8T patent/DK2024350T3/da active
- 2007-05-18 WO PCT/EP2007/054843 patent/WO2007135106A1/fr not_active Ceased
- 2007-05-18 CA CA2652469A patent/CA2652469C/fr not_active Expired - Fee Related
-
2012
- 2012-05-08 US US13/466,530 patent/US9452991B2/en active Active
-
2016
- 2016-09-26 US US15/276,208 patent/US9974779B2/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| DK2024350T3 (da) | 2013-12-09 |
| FR2901273B1 (fr) | 2010-12-24 |
| CA2652469C (fr) | 2016-05-03 |
| EP2024350B1 (fr) | 2013-09-18 |
| US8207373B2 (en) | 2012-06-26 |
| US20170079968A1 (en) | 2017-03-23 |
| JP5399237B2 (ja) | 2014-01-29 |
| MX2008014771A (es) | 2008-11-28 |
| US9974779B2 (en) | 2018-05-22 |
| US20180021318A9 (en) | 2018-01-25 |
| US20090209586A1 (en) | 2009-08-20 |
| US20120220633A1 (en) | 2012-08-30 |
| US9452991B2 (en) | 2016-09-27 |
| WO2007135106A1 (fr) | 2007-11-29 |
| JP2009537595A (ja) | 2009-10-29 |
| CN101466693B (zh) | 2012-12-12 |
| PT2024350E (pt) | 2013-12-11 |
| EP2024350A1 (fr) | 2009-02-18 |
| ES2436772T3 (es) | 2014-01-07 |
| CA2652469A1 (fr) | 2007-11-29 |
| AR061027A1 (es) | 2008-07-30 |
| FR2901273A1 (fr) | 2007-11-23 |
| CN101466693A (zh) | 2009-06-24 |
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